5-Methoxyindoleacetic acid → 1-[(5-methoxy-1H-indol-3-yl)methylcarbonyl]-4-(4-nitrophenyl)-piperazine

HRID 987023

反応式

HRID 987023 の反応式
C(N1C=CN=C1)(N1C=CN=C1)=O.[CH3:13][O:14][C:15]1[CH:16]=[C:17]2[C:21](=[CH:22][CH:23]=1)[NH:20][CH:19]=[C:18]2[CH2:24][C:25]([OH:27])=O.[N+:28]([C:31]1[CH:36]=[CH:35][C:34]([N:37]2[CH2:42][CH2:41][NH:40][CH2:39][CH2:38]2)=[CH:33][CH:32]=1)([O-:30])=[O:29]>C1COCC1.CN(C=O)C>[CH3:13][O:14][C:15]1[CH:16]=[C:17]2[C:21](=[CH:22][CH:23]=1)[NH:20][CH:19]=[C:18]2[CH2:24][C:25]([N:40]1[CH2:41][CH2:42][N:37]([C:34]2[CH:33]=[CH:32][C:31]([N+:28]([O-:30])=[O:29])=[CH:36][CH:35]=2)[CH2:38][CH2:39]1)=[O:27]

参加物

6

反応物 3

HCID 189865-Methoxyindoleacetic acidHCID 682631,1'-CarbonyldiimidazoleHCID 804471-(4-Nitrophenyl)piperazine

生成物 1

HCID 219187071-[(5-methoxy-1H-indol-3-yl)methylcarbonyl]-4-(4-nitrophenyl)-piperazine収率 91%

試薬・触媒・溶媒 2

HCID 6228Dimethylformamide溶媒HCID 8028Tetrahydrofuran溶媒

実験手順

In a 100 ml flask, 1.62 g (10 mmoles) of 1.1′-carbonyl-diimidazole is added to a solution of 2.05 g (10 mmoles) of 5-methoxyindole-3-acetic acid in 10 ml of THF. After one hour of agitation at ambient temperature, a solution of 1-(4-nitrophenyl)piperazine in 10 ml of DMF is added dropwise. Agitation is continued for 15 hours. The reaction medium is then concentrated under vacuum and the evaporation residue is precipitated from 50 ml of an ethyl acetate/water mixture (1/1). After filtration, the solid is rinsed successively with 50 ml of water, 50 ml of ethyl acetate and 50 ml of dichloromethane. After drying under vacuum, a yellow powder is obtained with a yield of 91%. Melting point: 239-240° C.

後処理

  1. waitAgitation is continued for 15 hours
  2. concentrationThe reaction medium is then concentrated under vacuum
  3. customthe evaporation residue is precipitated from 50 ml of an ethyl acetate/water mixture (1/1)
  4. filtrationAfter filtration
  5. washthe solid is rinsed successively with 50 ml of water, 50 ml of ethyl acetate and 50 ml of dichloromethane
  6. customAfter drying under vacuum
  7. customa yellow powder is obtained with a yield of 91%

出典と根拠

ORDレコード
ord-ac404678a13541dc8ad5ff7a0c2b08eb
出典データセット
uspto-grants-2003_10
特許番号
US06630461B2

関連ノート

読み込み中…